Adrianne Jeffries makes a strong case for how out-of-touch the crossword often seems these days:

…the Times crosswords, which have been edited by the famed crossword giant Will Shortz since 1993, are vexing for how outdated some of the clues and answers are, especially since in some cases the terms have been abandoned by the paper itself. The puzzle clearly isn’t seeking new talent or a new audience, and in its stodginess, it becomes clear that it is composed for a very particular reader with a very particular view of the world.

She backs up her supposition with numerous examples of tone-deaf cluing and grid fill, like ESKIMO, Oriental, and SISSIES.

There is some overlap with Ruth Graham’s points from last year — including the reductive use of HOMIE regarding black culture and the clue “One caught by the border patrol” for ILLEGAL — and Jeffries went on to include examples of the issue I raised last year with the objectionable “This, to Juan” cluing style that abounds in crosswords.

But she takes things one step further than previous efforts by pointing out how the crossword is out-of-step with the rest of the New York Times newspaper, citing the year that various terms were marked offensive in the Times style guide. (“Oriental” as a descriptor, for instance, was banned in 1999.)

It’s disheartening that articles like this are so necessary. Women and people of color deserve better representation in the Times puzzles, both as contributors of puzzles AND as subjects of clues and entries themselves.

I also found an exchange from 2011 illuminating. Shortz asked puzzle constructor Elizabeth Gorski to change an answer on her submitted puzzle. “There was one thing about the construction I didn’t like, and that was at 35 Down,” Shortz told The Atlantic. “The answer was LORELAI, and the sirens on the Rhine are of course ‘Lorelei,’ with an ‘e-i.’ Liz’s clue was Rory’s mom on Gilmore Girls, and I didn’t think solvers should have to know that.” He had the constructor revise the answer to make it 1) more old and 2) refer to mythical women who are so distractingly beautiful that they cause men to crash their ships on the rocks, instead of, a cool mom from a television show that millions of women (and some men) love.

Even as a (relatively) younger voice in puzzles, I can’t deny many of her points. Puzzles should do a better job of acknowledging modern culture, of serving as a tiny, daily time capsule of our world.

As I said last year, crosswords are a cultural microcosm, representing the commonalities and peculiarities of our language in a given time and place. They represent our trivia, our understanding, our cleverness, our humor, and, yes, sometimes our shortcomings.

One year later, I wonder if progress will continue to feel so gradual, or if, sometime soon, we’ll begin to feel the cultural quakes and shifts that indicate real change is approaching.

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Last week, a fellow puzzler passed along this link, which had an intriguing premise. The folks at BuzzFeed asked prominent crossword constructors to contribute their favorite tricky or misleading crossword clues, challenging the audience to puzzle out as many of them as possible.

There are 14 tricky clues, each with either some crafty wordplay or some delightfully wicked humor attached.

Now, fair warning, some of these are a bit risque (one drops the f-bomb), but they will all put your puzzly skills to the test.

[I wonder how Nancy Drew would do…]

My personal favorites were “Journey accompanier, often [9 letters]” and “Michigan county I promise never to use in a crossword again [6 letters],” both of which involve a level of honesty and pop culture awareness that transcends standard crossing cluing.

I managed to riddle out 10 of the 14 clues. Some of them were vague enough to allow for multiple answers — you don’t have a grid or crossing entries to help you limit options, after all — so I gave myself credit if the correct answer was one of several that came to mind.

How did you do on this crafty BuzzFeed challenge, PuzzleNationers? Let me know! I’d love to hear from you!

We’re reaching out to puzzle constructors, video game writers and designers, board game creators, writers, filmmakers, musicians, and puzzle enthusiasts from all walks of life, talking to people who make puzzles and people who enjoy them in the hopes of exploring the puzzle community as a whole.

And I’m overjoyed to have Matt Gaffney as our latest 5 Questions interviewee!

Matt Gaffney is a puzzle constructor, and over the last twenty-five years — fifteen as a full-time constructor! — he has made a name for himself as one of the most innovative names in crosswords. Whether it’s his signature Weekly Crossword Contest puzzles or the crossword murder mystery he launched on Kickstarter, he’s become synonymous with puzzles that contain a little something extra.

In addition to puzzle books and books about puzzles, he’s been published in The New York Times, The Washington Post, Slate Magazine, and GAMES Magazine, among numerous others. All told, he estimates he’s created more than 4,000 puzzles in his career!

Matt was gracious enough to take some time out to talk to us, so without further ado, let’s get to the interview!

5 Questions for Matt Gaffney

1.) How did you get started with puzzles?

My older sister starting bringing home Dell and Penny Press puzzle magazines when I was about 8 or 9. I have a hypercompetitive personality with certain things, and puzzles turned out to be one of them, so I starting submitting crosswords to Dell Champion. They ran my first two published puzzles when I was 13.

2.) In addition to your daily crossword puzzles, you host a Weekly Crossword Contest, featuring crosswords with a puzzle-within-a-puzzle lurking inside. These “metapuzzles” have grown in popularity over the years. What separates a quality metapuzzle from a bonus answer that simply feels tacked on? What are some of your favorite past metapuzzles?

Ideally a metapuzzle is like a good hiding place in hide-and-go-seek. The seeker shouldn’t find you right away; they should overlook you a couple of times, walk past you a couple of times, and only later say, “Ah, I should’ve found you sooner.”

My favorite meta that I myself wrote in the past year is called “Corporate Structure” and can be found here.

My favorite meta that someone else wrote is called “Seasonal Staff” by Francis Heaney and you can buy it for $1 here (under “Puzzle” scroll down to 2013-12-18).

[Just one of many puzzle-themed titles Matt has authored.]

3.) When you celebrated 5 years of your Weekly Crossword Contest, you stated that MGWCC will run for 1,000 weeks, which would put the final edition around August 6, 2027. Do you have any predictions for how crosswords might have changed by then?

I think by then individual crossword writers will be more brandable than we are now. With a few exceptions like Merl Reagle, familiar crossword brands are still usually publications or, in the case of Will Shortz, an editor.

The Web has allowed constructors like myself, Brendan Quigley, Liz Gorski, Erik Agard, and many others to get our work out independently, so I think solvers will move more towards seeking out their favorite individual constructors rather than solving newspaper puzzles. Sort of like how you can buy an album by your favorite artist instead of waiting for them to play on the radio.

4.) What’s next for Matt Gaffney?

I’m going to market my Daily Crossword this summer. I’ve been too busy to find a good home for it but the number of hits it gets, with zero marketing on my part, is amazing to me.

5.) If you could give the readers, writers, puzzle fans, and aspiring constructors in the audience one piece of advice, what would it be?

I would encourage people to explore the indie crosswords. If the newspaper dailies are ABC, NBC, and CBS, then the independent puzzle writers are HBO and Showtime. Go here and click on any of the names on the bottom-left sidebar and see what’s good.

Not all of them are indie crossword sites (some are crossword critique sites, some are other crossword-related stuff) but about half of them are personal sites of independent crossword writers.

We’re reaching out to puzzle constructors, video game writers and designers, writers, filmmakers, and puzzle enthusiasts from all walks of life, talking to people who make puzzles and people who enjoy them in the hopes of exploring the puzzle community as a whole.

And I’m excited to have Robin Stears as our latest 5 Questions interviewee!

Robin is a puzzle constructor whose crosswords appear not only on her StearsWords site, but have also appeared in Penny Press/Dell and Kappa titles as well as the Los Angeles Times. Her puzzles are clever and topical, often striving to add new entries and wrinkles to the field of crossword construction and cluing.

Robin was gracious enough to take some time out to talk to us, so without further ado, let’s get to the interview!

5 Questions for Robin Stears

1.) How did you get started with puzzles?

Crossword puzzles and word games have always appealed to me, and after my first daughter was born, I was looking for a way to work at home. My mom suggested the idea of constructing crossword puzzles, since I’d been killing time solving them while I was wondering what to do. Armed with a stack of dictionaries, graph paper, and pencils, I created a puzzle, and typed it on my mom’s typewriter, and colored in the black squares with a marker. I sent my first puzzle to Janis Weiner at Kappa, who promptly sent it back with a bunch of notes. I’m very grateful to her for taking the time to explain what I did wrong. It’s because of her I decided to try again. She rejected most of my puzzles at first, but she always explained why. I consider her my mentor, but she probably doesn’t know that.

2.) You recently constructed a puzzle utilizing that most infamous of cinematic weather phenomena, the sharknado. You have a knack for releasing topical puzzles steeped in pop culture. Is this more a case of keeping your puzzles fresh (since so many crosswords slip into archaic terms and dated references), or of you constructing the kinds of puzzles you’d enjoy solving?

It’s a little bit of both. I think language is fluid and crossword puzzles should reflect that. For example, the word “inception” wasn’t quite as popular in everyday conversation prior to the 2010 movie release as it is today. I don’t know about other constructors, but I find it very satisfying to be the first to use a new word in a crossword puzzle; I suspect they do, too, as evidenced by the number of times ZZZQUIL was used in puzzles when that product was introduced.

The fandom crossword puzzles were born from a comment I saw on Tumblr; someone complained that there weren’t any fandom puzzles. It occurred to me that the only specialty puzzle — where all the clues refer to a single theme — was the Bible puzzle, probably because there are nearly 600,000 words in it. There are about the same number of words in the Lord of the Rings books, though.

Nearly every fandom has a wiki, and a plethora of trivia websites, and by exploring them — along with the Internet Movie Database, Wikipedia, Reddit, and other sources, I was able to create several puzzles specifically for certain fandoms, including both Star Wars and Star Trek, “Adventure Time,” and “Doctor Who.” There is so much information online, that I was actually able to create the “Doctor Who” puzzle without having seen a single episode! My younger daughter’s a big fan, though; she inspired the “Adventure Time” one, too. They also allow me to pay homage to the things I love, like Stephen Colbert, Syfy movies, Donkey Kong, and the US Postal Service.

Every constructor’s style is a little different, and like most solvers, I have my favorites — Liz Gorski, Tyler Hinman, Brendan Emmett Quigley, Merl Reagle, Matt Gaffney, Trip Payne, and of course, Patrick Blindauer, whose dollar bill crossword puzzle is my personal all-time favorite. We all put our personal stamp on the puzzles we create. But, the modern crossword puzzle is about to turn one hundred years old, and if they’re going to remain relevant in the modern world, they have to change and adapt to suit younger solvers. That means constructors need to use the Urban Dictionary as well as Webster’s.

3.) You’re also a published author with several titles to your credit. How does the creative process for writing a book compare to that of creating a crossword?

Writing fiction and writing crossword clues are completely different processes. A novel is a long, leisurely cross-country trip, while a crossword clue is a quick peek around the corner. It took me about a year to write each book, after researching it for months, and another six months of editing. Crossword puzzles may take anywhere from an hour to a day to complete, depending on the size and the theme entries. In the past few years, partly for the instant gratification, partly because it’s more lucrative, and partly because it’s more fun, I’ve concentrated more on crossword puzzles, although I do have another novel I intend to finish.

4.) What’s next for Robin Stears?

Well, there’s that novel… eventually. In the meantime, I’d like to attend more puzzle events, like Lollapuzzoola and the American Crossword Puzzle Tournament. Last year, I volunteered at my local tournament, and it was fun meeting the participants and discussing the puzzles they’d solved — there’s no substitute for immediate feedback. Solving crosswords is very different from constructing them. I have a database at my disposal, and I have great respect for solvers who have to remember all those clues! I’d like to meet the constructors I admire to exchange ideas and hear their stories, and Amy Reynaldo and Kathy Matheson (Crossword Kathy), whose blogs are so informative and whose ideas and opinions I respect — it’s because of Amy’s “Diary of a Crossword Fiend” blog that I removed certain words from my database, like APER. I’d love to finally meet the people behind PuzzleNation, Cruciverb, Sporcle, and Quinapalus, and all the other puzzle-related sites. Constructing crosswords is a lonely business — I need to get out more.

The fandom trivia puzzles are a challenge, so you’ll probably see more of those. Fans of “Breaking Bad” will see a special puzzle at the end of September for the final episode, and baseball trivia fans can expect their puzzle in October, during the World Series. For Halloween, I’m planning a horror movie puzzle, and of course, I’ll do something for the 100th anniversary of crosswords in December — I’m open to ideas for that one.

Ben Tausig recently pointed out in an article in “The Hairpin” that there seem to be fewer women constructors, and I’d love to help remedy that. When I first started, twenty-odd years ago, constructing a crossword puzzle was difficult and time-consuming — these days, most constructors use software with a built-in database of words and clues. My personal choice is Crossword Compiler. I think anyone with a basic knowledge of the rules and a bit of computer savvy could create and publish a crossword puzzle. I believe there’s plenty of room in the crossword puzzle world for new constructors with new ideas. Technology and the opportunities for puzzle creators and solvers to interact with one another will change the ways crosswords are created. I had a lot of help in the beginning, and I hope to pay it forward to the next generation of crossword constructors.

[[Glenn’s sidenote: Robin also had a lot of interesting points regarding the move toward digital puzzle distribution, and I think that topic deserves a post of its own. Keep your eyes peeled for that post (and her thoughtful comments) in the near future!]]

5.) If you could give the readers, writers, and puzzle fans in the audience one piece of advice, what would it be?

When I construct a crossword puzzle, I always have the fans in mind. I want to create a solving experience that’s fun and enjoyable for them. The entire time I was constructing a special “420” puzzle, which, to my knowledge, had never been done before, I was imagining how surprised and delighted some puzzle solvers would be that week. And like the Super Bowl puzzle and the Harry Potter puzzle, I knew that not everybody would appreciate it, but the ones who did would appreciate it all the more because I constructed it especially for them.

When I construct puzzles for Penny Press/Dell, I also have a certain fan in mind — someone who enjoys an easier solve, with a little less pop culture and a little more word play. No matter which publisher I’m targeting, I’m always thinking about the puzzle solvers and what they might enjoy. Frequently, I construct customized crossword puzzles as gifts; they’re always a big hit because they’re personal.

So, my advice is this: Tell me what you want! Send me an email, tweet me, write on my Facebook or Google+, hit me up on Blogger or Tumblr — StearsWords is not hard to find. I maintain a variety of social media because I want puzzle fans of all kinds to interact with me. Much of my day is spent scanning social sites like Twitter, Pinterest, and Reddit and reading puzzle blogs, trying to find out what kinds of topics might interest puzzle solvers. Anyone can send me an idea for a puzzle, and if I like it, I’ll do my best to make it happen. I’d rather give puzzle fans what they really want than give them what I want them to have and hope they like it.

Many thanks to Robin Stears for her time. Check out her StearsWords puzzles on her website, and follow her on Twitter (https://twitter.com/RobinStears)! I can’t wait to see what puzzly goodness she cooks up for us next.